Technical Abstract:
The utilization of excess glycerol supplies derived from the burgeoning biodiesel industry is of major importance to the oleochemical industry as the economic viability of the biodiesel and oleochemical industries are closely linked to glycerol prices. Carbonate compounds based on glycerol, such as glycerol carbonate, are gaining prominence due to its simple preparation, interesting properties and chemistry. The synthesis, physical properties, and chemistry of an interesting glycerol-based carbonate (4, bis[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl] carbonate) is presented. This carbonate was prepared in 65-70% isolated yields by an interchange reaction between isopropylidene glycerol (solketal) and diethyl carbonate in the presence of sodium methoxide catalyst. The carbonate was characterized using Fourier transform infrared spectroscopy (FTIR), 1H and 13C nuclear magnetic resonance spectroscopy (NMR), and gas chromatography-mass spectrometry (GC/MS). Physical properties of the carbonate such as kinematic viscosity, refractive index, melting point, as well as the lubricity were determined. Hydrolysis of carbonate’s isopropylidene groups gave the corresponding polyol (6, bis(2,3-dihydroxypropyl) carbonate) in yields of 84%. The polyol carbonate was characterized by 1H and 13C NMR and represents a potentially interesting polyol.